EP0156310A2 - Procédé pour réagir des oléfines et de l'anhydride maléique et utilisation d'anhydride succinique obtenu pour la préparation des inhibiteurs de corrosion et des additifs pour les huiles minérales - Google Patents

Procédé pour réagir des oléfines et de l'anhydride maléique et utilisation d'anhydride succinique obtenu pour la préparation des inhibiteurs de corrosion et des additifs pour les huiles minérales Download PDF

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Publication number
EP0156310A2
EP0156310A2 EP85103306A EP85103306A EP0156310A2 EP 0156310 A2 EP0156310 A2 EP 0156310A2 EP 85103306 A EP85103306 A EP 85103306A EP 85103306 A EP85103306 A EP 85103306A EP 0156310 A2 EP0156310 A2 EP 0156310A2
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EP
European Patent Office
Prior art keywords
maleic anhydride
reaction
olefin
mineral oil
average molecular
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP85103306A
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German (de)
English (en)
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EP0156310A3 (en
EP0156310B1 (fr
Inventor
Klaus Dr. Bronstert
Hans-Henning Dr. Vogel
Hans Peter Dr. Rath
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BASF SE
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BASF SE
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Publication date
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Publication of EP0156310A2 publication Critical patent/EP0156310A2/fr
Publication of EP0156310A3 publication Critical patent/EP0156310A3/de
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Publication of EP0156310B1 publication Critical patent/EP0156310B1/fr
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/54—Preparation of carboxylic acid anhydrides
    • C07C51/567—Preparation of carboxylic acid anhydrides by reactions not involving carboxylic acid anhydride groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/46—Reaction with unsaturated dicarboxylic acids or anhydrides thereof, e.g. maleinisation
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
    • C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
    • C10M129/26—Carboxylic acids; Salts thereof
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
    • C10M129/86—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of 30 or more atoms
    • C10M129/92—Carboxylic acids
    • C10M129/93—Carboxylic acids having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
    • C23F—NON-MECHANICAL REMOVAL OF METALLIC MATERIAL FROM SURFACE; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL; MULTI-STEP PROCESSES FOR SURFACE TREATMENT OF METALLIC MATERIAL INVOLVING AT LEAST ONE PROCESS PROVIDED FOR IN CLASS C23 AND AT LEAST ONE PROCESS COVERED BY SUBCLASS C21D OR C22F OR CLASS C25
    • C23F11/00—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent
    • C23F11/08—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids
    • C23F11/10—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids using organic inhibitors
    • C23F11/12—Oxygen-containing compounds
    • C23F11/124—Carboxylic acids
    • C23F11/126—Aliphatic acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2810/00—Chemical modification of a polymer
    • C08F2810/30—Chemical modification of a polymer leading to the formation or introduction of aliphatic or alicyclic unsaturated groups
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/121—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms
    • C10M2207/123—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms polycarboxylic
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/129—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of thirty or more carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/22—Acids obtained from polymerised unsaturated acids

Definitions

  • the invention relates to a process for reacting olefinically unsaturated hydrocarbons, in particular dimeric to polymeric isobutene derivatives, which have an average molecular weight with a number average M from 100 to 3000, with maleic anhydride in a molar ratio of maleic anhydride to olefin from 0.2 to 3.0 in Presence of 1 to 5000 ppm by weight, based on the olefin, of an additive preventing side reactions at temperatures between 150 and 280 ° C. to form the corresponding succinic anhydrides and their use for the preparation of corrosion inhibitors or mineral oil auxiliaries.
  • the object of the invention is to avoid the disadvantages mentioned above and to find a process for the adduct-forming reaction of olefins with maleic anhydride in which the conversion is accelerated, the yield is increased and the resin formation of the maleic anhydride is reduced.
  • alkoxides of titanium, zirconium, vanadium or aluminum are used as additives which prevent the side reactions in the process described at the outset.
  • C 2 to C 4 alkoxides are preferably used.
  • Suitable olefinically unsaturated hydrocarbons are all compounds and their mixtures which have terminal or internal double bonds and have an average molecular weight (M u ) between 100 and 3000.
  • Olefinically unsaturated hydrocarbons are understood to mean in particular monomeric, oligomeric or polymeric C 8 -C 14 -alkenes, the chains of which may be branched and which have an average molecular weight (counting mean) M n of 100 to 3000, the average molecular weight M n with The osmotic pressure of the chloroform solution can be determined.
  • the olefinically unsaturated hydrocarbons which are subjected to the addition reaction include, for example, 1-octene, 2-methylpentene, 2-methyl-5-propyl-1-hexene, 3-cyclohexyl-1-butene or the oligomers of C 2 - to C 20 - olefins, for example the oligomers of ethylene, propylene, 1-butene, isobutene, 1-hexene, 1-octene ect. as well as the polyisobutenes with M u from 250 to 3000 and the diisobutene.
  • olefinically unsaturated hydrocarbons are dimeric to polymeric isobutene derivatives, ie diisobutene, oligomeric isobutenes with M n between 200 and 350 and polymeric isobutenes with M n between 250 and 3000.
  • polymeric isobutene derivatives ie diisobutene
  • oligomeric isobutenes with M n between 200 and 350
  • polymeric isobutenes with M n between 250 and 3000.
  • the reaction of the olefinically unsaturated hydrocarbons with maleic anhydride is carried out in a molar ratio, i.e. in the molar ratio, based on moles of the components, maleic anhydride to olefin from 0.2 to 3.0, preferably 0.5 to 2.0.
  • a process is particularly preferred in which equimolar amounts of olefin and maleic anhydride can be used.
  • the reaction is carried out in the presence of 1 to 5000, preferably 5 to 1000, ppm by weight, based on the olefin used, of an additive which is intended to accelerate the desired addition reaction.
  • additives are known, as mentioned at the beginning. They bring about a reduction in the reaction time and an increase in the degree of conversion of the particular olefin.
  • the main side reaction to be mentioned is the formation of polymaleic anhydride, which is obtained as a solid residue, or polymaleic anhydride with an olefinic fraction from free-radical copolymerization of olefin and maleic anhydride, which is usually obtained in the form of a sticky resin.
  • the addition reaction to form the corresponding succinic anhydrides takes place in the heat at temperatures between 150 and 280, preferably 180 and 230 ° C.
  • the reaction itself can be carried out in a stirred autoclave, a solvent is not required.
  • the reaction times are usually up to 20 hours.
  • the procedure is such that a pressure between 5 and 1000, preferably 5 and 100 mbar is set in the reaction vessel at the start of the reaction.
  • a pressure of 1 to 10 bar prevails in the reaction zone after heating up to the reaction temperature.
  • a nitrogen or carbon dioxide atmosphere is preferably used as the inert atmosphere.
  • the mixture is allowed to cool and the reaction mass is preferably worked up by distillation. If possible, the reactants should be anhydrous.
  • alkoxides preferably the C 2 -C 4 -alkoxides, of titanium, zirconium, vanadium or aluminum are to be used as additives.
  • Such compounds are known per se and are listed, for example, in the Alfa Catalog 1981 from Ventrum GmbH, Zeppelinstrasse 7, D-7500 Düsseldorf 1 as so-called Alfa products.
  • the alkoxides mentioned are in the liquid state, optionally as a complex compound with the corresponding alcohol, and are used in this form in the addition reaction. They are used with a degree of purity of 95 to 99% by weight, and in the case of the alkoxides of aluminum from 90 to 99% by weight.
  • the alkoxides to be used are soluble in the reaction mixture.
  • the maleinized olefin reaction products obtained with average molecular weights (M n ) of 200 to 350 are used for the production of anti-corrosion agents for aqueous or organic systems.
  • the resulting olefin succinic anhydrides with average molecular weights (M) of 250 to 3000 can be converted in a simple manner into compounds which are suitable as mineral oil auxiliaries such as lubricant additives. For this purpose, they can be converted into the corresponding esters with polyhydric alcohols or into the corresponding salts, amides or imides with amines, which are then mixed in, for example in lubricating oils (cf. GB-A-1 483 729 and GB-A-2 081 274). Such methods are known so that they do not have to be explained further here.
  • 500 g polyisobutene (M n 930), 50 g maleic anhydride and 500 ppm titanium (IV) n-butoxide [Ti (C 4 H 9 0) 4 ] are in a 1 1 autoclave made of V2A steel, which is stirred with magnetic sticks , submitted, flushed with nitrogen, evacuated to 2 mbar and then heated in an oil bath to 225 ° C with vigorous stirring. After 4 h at 225 ° C., the reactor is depressurized and unreacted maleic anhydride (MA) is separated off by distillation at a vacuum of 2 mbar.
  • MA unreacted maleic anhydride
  • the remaining reaction mixture contains 40% by weight of unreacted polyisobutene (PIB) and 60% by weight of polyisobutenyl succinic anhydride (PIBSA).
  • PIB polyisobutene
  • PIBSA polyisobutenyl succinic anhydride
  • the analysis is carried out by preparative, column chromatography separation with silica gel as adsorbent, hexane as eluent for PIB and toluene / acetone in a weight ratio of 9: 1 for PIBSA.
  • the final double bond share of the unreacted PIB is 14%.
  • a residue in solid or resinous form is not found in the product. Deposits can only be found on the stirrer and walls, which are removed by toluene washing in acetone after removal of PIB and PIBSA.
  • the solution is transferred to a flask, evaporated and the residue is determined gravimetrically. It is less than 0.2 g.
  • a technical mixture of 2,4,4-trimethylpentene (1) and - (2) is mixed with 500 ppm titanium (IV) n-butoxide [Ti (C 4 H 9 0) 4 ] in a 1 1 V2A autoclave is stirred with magnetic sticks, submitted, flushed with nitrogen, evacuated to 15 mbar and then heated to 225 ° C. in an oil bath.
  • 350 g MSA are added at a rate of 100 g / h and a starting quantity of 50 g using a metering pump. After 3 hours this addition is complete and the batch is allowed to react for 4 hours. After cooling, the mixture is filtered and the residue is washed carefully with toluene and dried.
  • the reaction vessel is also rinsed with toluene and the remaining coating is dissolved in acetone and evaporated in a small flask.
  • the sum of the return Filtration and evaporation levels are less than 0.2 g.
  • the olefin conversion is 70 Gew.X and is determined by distillation, the MSA conversion is quantitative.
  • the proportion of residual olefin in 2,4,4-trimethylpentene (1) is 33% by weight.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Materials Engineering (AREA)
  • Mechanical Engineering (AREA)
  • Metallurgy (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Furan Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Preventing Corrosion Or Incrustation Of Metals (AREA)
EP85103306A 1984-03-29 1985-03-21 Procédé pour réagir des oléfines et de l'anhydride maléique et utilisation d'anhydride succinique obtenu pour la préparation des inhibiteurs de corrosion et des additifs pour les huiles minérales Expired EP0156310B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19843411531 DE3411531A1 (de) 1984-03-29 1984-03-29 Verfahren zur umsetzung von olefinen mit maleinsaeureanhydrid und verwendung der erhaltenen bernsteinsaeureanhydride zur herstellung von korrosionsschutzmitteln und mineraloelhilfsmitteln
DE3411531 1984-03-29

Publications (3)

Publication Number Publication Date
EP0156310A2 true EP0156310A2 (fr) 1985-10-02
EP0156310A3 EP0156310A3 (en) 1986-04-23
EP0156310B1 EP0156310B1 (fr) 1987-10-28

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EP85103306A Expired EP0156310B1 (fr) 1984-03-29 1985-03-21 Procédé pour réagir des oléfines et de l'anhydride maléique et utilisation d'anhydride succinique obtenu pour la préparation des inhibiteurs de corrosion et des additifs pour les huiles minérales

Country Status (5)

Country Link
US (1) US4599433A (fr)
EP (1) EP0156310B1 (fr)
JP (1) JPS60222473A (fr)
CA (1) CA1226293A (fr)
DE (2) DE3411531A1 (fr)

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7498386B2 (en) 2002-10-11 2009-03-03 Basf Se Derivatives of polymers for permanent modification of hydrophobic polymers
US7767748B2 (en) 2004-02-13 2010-08-03 Basf Aktiengesellschaft Aqueous polymer dispersions containing amphiphilic block copolymers, method for producing said dispersions and the use thereof
WO2011073222A2 (fr) 2009-12-18 2011-06-23 Basf Se Polyesters hyperramifiés à noyau hydrophobe pour la solubilisation d'agents actifs peu solubles
WO2011073220A1 (fr) 2009-12-18 2011-06-23 Basf Se Polyesters hyperramifiés à noyau hydrophobe pour la solubilisation d'agents actifs peu solubles
WO2012029038A1 (fr) 2010-09-01 2012-03-08 Basf Se Amphiphile servant à solubiliser des substances actives difficilement solubles
EP3257874A1 (fr) 2016-06-15 2017-12-20 Basf Se Dérivé d'acide alcénylsuccinique et son procédé de préparation
WO2017216023A1 (fr) 2016-06-15 2017-12-21 Basf Se Agent antichoc à base de polyisobutylène pour polyamides
WO2018007192A1 (fr) 2016-07-05 2018-01-11 Basf Se Inhibiteurs de corrosion pour carburants et lubrifiants
WO2018007191A1 (fr) 2016-07-05 2018-01-11 Basf Se Utilisation d'inhibiteurs de corrosion pour carburants et lubrifiants
US11085001B2 (en) 2015-07-16 2021-08-10 Basf Se Copolymers as additives for fuels and lubricants
US11634654B2 (en) 2014-01-29 2023-04-25 Basf Se Polycarboxylic acid-based additives for fuels and lubricants
WO2023198589A1 (fr) 2022-04-14 2023-10-19 Basf Se Procédé de fabrication d'anhydrides succiniques de polyisobutène
WO2023198616A1 (fr) 2022-04-14 2023-10-19 Basf Se Procédé de fabrication d'anhydrides succiniques de polyisobutène

Families Citing this family (12)

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GB8611772D0 (en) * 1986-05-14 1986-06-25 Ici Plc Corrosion inhibitor compositions
US4879394A (en) * 1987-11-13 1989-11-07 Shell Oil Company Reaction of olefins with maleic anhydride
US4761488A (en) * 1987-11-13 1988-08-02 Shell Oil Company Reaction of olefins with maleic anhydride
USH917H (en) 1989-07-28 1991-05-07 Shell Oil Company Polymer blend
GB9309121D0 (en) * 1993-05-04 1993-06-16 Bp Chem Int Ltd Substituted acylating agents
US5777025A (en) * 1996-02-09 1998-07-07 Exxon Chemical Patents Inc. Process for preparing polyalkenyl substituted C4 to C10 dicarboxylic acid producing materials
US5891953A (en) * 1996-02-09 1999-04-06 Exxon Chemical Patents Inc Process for preparing polyalkenyl substituted mono- and dicarboxylic acid producing materials (PT-1302)
US6228978B1 (en) 1997-06-25 2001-05-08 Exxon Mobil Chemical Patents Inc Star-branched polymer with dendrimer core
US6545101B2 (en) 1997-06-25 2003-04-08 Exxonmobil Chemical Patents Inc. Star-branched polymer with dendrimer core
DE10232747A1 (de) * 2002-07-18 2004-02-05 Basf Ag Verwendung von Polyisobutylen-Derivaten zur Behandlung von Metalloberflächen
CA2602378C (fr) 2005-03-28 2014-01-28 The Lubrizol Corporation Composes et complexes de titane comme additifs dans des lubrifiants
WO2017009306A1 (fr) * 2015-07-16 2017-01-19 Basf Se Inhibiteurs de corrosion pour carburants et lubrifiants

Citations (1)

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US2768175A (en) * 1952-01-29 1956-10-23 Eastman Kodak Co Catalytic process for the conversion of isodehydroacetic esters into derivatives of beta-methyl glutaconic acid

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US3855251A (en) * 1972-12-22 1974-12-17 Standard Oil Co Alkenyl-substituted succinic anhydride
US3953475A (en) * 1973-05-10 1976-04-27 Standard Oil Company Polybutene composition containing halo-carbonyl additives
US3935249A (en) * 1973-05-10 1976-01-27 Standard Oil Company Tar reduction by inorganic halide for reaction of unsaturated anhydride and polybutene
FR2273014B1 (fr) * 1974-05-31 1978-01-20 Rhone Poulenc Ind
US4278604A (en) * 1979-08-27 1981-07-14 Texaco Inc. Process for preparing an alkenyl-substituted dicarboxylic acid anhydride
GB2081274A (en) * 1980-08-06 1982-02-17 Orobis Ltd Polyalkenyl bis(succinic acids or anhydrides)
US4388471A (en) * 1982-04-30 1983-06-14 Chevron Research Company Process for the preparation of alkenyl succinic anhydrides

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US2768175A (en) * 1952-01-29 1956-10-23 Eastman Kodak Co Catalytic process for the conversion of isodehydroacetic esters into derivatives of beta-methyl glutaconic acid

Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7498386B2 (en) 2002-10-11 2009-03-03 Basf Se Derivatives of polymers for permanent modification of hydrophobic polymers
US7767748B2 (en) 2004-02-13 2010-08-03 Basf Aktiengesellschaft Aqueous polymer dispersions containing amphiphilic block copolymers, method for producing said dispersions and the use thereof
WO2011073222A2 (fr) 2009-12-18 2011-06-23 Basf Se Polyesters hyperramifiés à noyau hydrophobe pour la solubilisation d'agents actifs peu solubles
WO2011073220A1 (fr) 2009-12-18 2011-06-23 Basf Se Polyesters hyperramifiés à noyau hydrophobe pour la solubilisation d'agents actifs peu solubles
WO2012029038A1 (fr) 2010-09-01 2012-03-08 Basf Se Amphiphile servant à solubiliser des substances actives difficilement solubles
US11634654B2 (en) 2014-01-29 2023-04-25 Basf Se Polycarboxylic acid-based additives for fuels and lubricants
US11085001B2 (en) 2015-07-16 2021-08-10 Basf Se Copolymers as additives for fuels and lubricants
EP3257874A1 (fr) 2016-06-15 2017-12-20 Basf Se Dérivé d'acide alcénylsuccinique et son procédé de préparation
WO2017216023A1 (fr) 2016-06-15 2017-12-21 Basf Se Agent antichoc à base de polyisobutylène pour polyamides
WO2017216022A1 (fr) 2016-06-15 2017-12-21 Basf Se Nouveaux dérivés d'acide alcényl-succinique et leurs procédés de préparation
US10731035B2 (en) 2016-06-15 2020-08-04 Basf Se Impact modifier based on polyisobutane for polyamides
WO2018007192A1 (fr) 2016-07-05 2018-01-11 Basf Se Inhibiteurs de corrosion pour carburants et lubrifiants
US11078418B2 (en) 2016-07-05 2021-08-03 Basf Se Corrosion inhibitors for fuels and lubricants
US10844308B2 (en) 2016-07-05 2020-11-24 Basf Se Corrosion inhibitors for fuels and lubricants
WO2018007191A1 (fr) 2016-07-05 2018-01-11 Basf Se Utilisation d'inhibiteurs de corrosion pour carburants et lubrifiants
WO2023198589A1 (fr) 2022-04-14 2023-10-19 Basf Se Procédé de fabrication d'anhydrides succiniques de polyisobutène
WO2023198616A1 (fr) 2022-04-14 2023-10-19 Basf Se Procédé de fabrication d'anhydrides succiniques de polyisobutène

Also Published As

Publication number Publication date
EP0156310A3 (en) 1986-04-23
EP0156310B1 (fr) 1987-10-28
CA1226293A (fr) 1987-09-01
DE3411531A1 (de) 1985-10-10
DE3560824D1 (en) 1987-12-03
US4599433A (en) 1986-07-08
JPH0529034B2 (fr) 1993-04-28
JPS60222473A (ja) 1985-11-07

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